Multi-step reaction with 10 steps
1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 4 h / 0 °C / Inert atmosphere
2.1: lithium borohydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere
3.1: triphenylphosphine; diethylazodicarboxylate; diphenyl phosphoryl azide / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere
4.1: water; triphenylphosphine / tetrahydrofuran / 12 h / 20 °C / Inert atmosphere
5.1: pyridine / dichloromethane / 2 h / 0 °C / Inert atmosphere
5.2: 2.08 h / 0 °C / Inert atmosphere
6.1: morpholine; tetrakis(triphenylphosphine) palladium(0) / dichloromethane / 1 h / 0 °C / Inert atmosphere; Darkness
7.1: acetic acid; sodium cyanoborohydride / ethanol / 4 h / 20 °C / Inert atmosphere
8.1: N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate / dichloromethane / 20 °C / Inert atmosphere
9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere
10.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0 - 20 °C / Inert atmosphere
With
morpholine; pyridine; lithium borohydride; tetrakis(triphenylphosphine) palladium(0); diphenyl phosphoryl azide; tetrabutyl ammonium fluoride; water; sodium cyanoborohydride; acetic acid; N-ethyl-N,N-diisopropylamine; triphenylphosphine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate; diethylazodicarboxylate;
In
tetrahydrofuran; ethanol; dichloromethane;
DOI:10.1002/ejoc.201301769